Showing metabocard for Lanosterin (BMDB0001251)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:04 UTC
Update Date2020-05-21 16:28:43 UTC
BMDB IDBMDB0001251
Secondary Accession Numbers
  • BMDB01251
Metabolite Identification
Common NameLanosterin
DescriptionLanosterin, also known as botalan base 138 or lanosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, lanosterin is considered to be a sterol lipid molecule. Lanosterin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta)-Lanosta-8,24-dien-3-olChEBI
(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-olChEBI
4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b)-Lanosta-8,24-dien-3-olGenerator
(3β)-Lanosta-8,24-dien-3-olGenerator
(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-olGenerator
4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-olGenerator
(3 beta)-Lanosta-8,24-dien-3-olHMDB
(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
Botalan base 138HMDB
Lanosta-8,24-dien-3-olHMDB
Lanosta-8,24-dien-3beta-olHMDB
Lanosta-8,24-dienolHMDB
LanosterolHMDB
LansterHMDB
4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-olMeSH, HMDB
KryptosterolMeSH, HMDB
LanosterinChEBI
3beta-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3beta-Hydroxylanosta-8,24-dieneHMDB
3β-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3β-Hydroxylanosta-8,24-dieneHMDB
4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-olHMDB
4,4,14α-Trimethylcholesta-8,24-dien-3β-olHMDB
5alpha-Lanosta-8,24-dien-3beta-olHMDB
5α-Lanosta-8,24-dien-3β-olHMDB
Lanosta-8,24-dien-3β-olHMDB
Lanostadien-3beta-olHMDB
Lanostadien-3β-olHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number79-63-0
SMILES
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
InChI KeyCAHGCLMLTWQZNJ-BQNIITSRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.72ALOGPS
logP7.71ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.54 m³·mol⁻¹ChemAxon
Polarizability55.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-2953300000-ae1832f19369485ff53cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aou-9820200000-573525b346ad3c9eef59View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2910000000-c67a1f122f33698a14f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0a6r-0110900000-5e42e1f2d9ad534c003cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0a4i-0230900000-10f58fa6e118cd7c5997View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-1791800000-178153ad92eececb33c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0a4i-2980300000-6ce95c7f8b15b35475afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-0a4j-2950100000-48f86ff7a22c596aa44dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0592-3940000000-c35d0cb6a2e4e291e8f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0592-3920000000-d717fdd3322a881bef99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-0592-4910000000-4c6d07e3a8e48ae88580View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0a4j-5900000000-4c8b72037dbeae9a46d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-067m-8900000000-522b8688d50362297c41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 62V, positivesplash10-0aou-9700000000-70d433827c1a6dab0c41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-05ox-9500000000-5b122dea636d3e3b5916View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, positivesplash10-05r3-9500000000-0c1c5cbd994f8406f30eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 111V, positivesplash10-05r3-9600000000-5cb8ae11d071fa19f206View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0ktf-0392000000-03cda521ce6e102d92e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-059j-2900000000-8086693fb040e5ed7501View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0a4i-4900000000-c58ff2dc28c6ba639997View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-01vk-0900000000-805937445cceda0cd70aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0aor-0900000000-22d304b445b737121aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-2cfcf7ce4b5b21140eaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-2139500000-9a25961000db9796d6daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4259100000-9f7f26265abec4122e35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-77a57cecc2069bee1926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-5b0f06bf8120e780e30cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-421e305d47b29da427d2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd687View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001251
DrugBank IDDB03696
Phenol Explorer Compound IDNot Available
FooDB IDFDB013802
KNApSAcK IDC00003657
Chemspider ID216175
KEGG Compound IDC01724
BioCyc IDLANOSTEROL
BiGG ID38253
Wikipedia LinkLanosterol
METLIN ID6108
PubChem Compound246983
PDB IDNot Available
ChEBI ID16521
References
Synthesis ReferenceMaienthal, Millard; Franklin, Philip J. Preparation of lanosterol from bromolanosterol. Journal of Organic Chemistry (1955), 20 1627-30.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol 14-alpha demethylase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP51A1
Uniprot ID:
Q4PJW3
Molecular weight:
56596.0
Reactions
Lanosterin + 3 Oxygen + 3 NADPH → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid +3 NADP +4 Waterdetails
Enzyme Details
2. Lanosterol synthase
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus. Through the production of lanosterol may regulate lens protein aggregation and increase transparency.
Gene Name:
LSS
Uniprot ID:
P84466
Molecular weight:
83184.0
Enzyme Details
3. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
Lanosterin + NADPH → 24,25-Dihydrolanosterol + NADPdetails